Carving portraits on pumpkins is quite fun and also quite time-consuming. Allow 6-8 hours over one or two days to complete each jack-o-lantern. You can use any picture you like- friends, family members, pets, etc.- I prefer to use images of celebrities because they're immediately recognizable to the general public. I simply find a picture online and use Photoshop to adjust it to an appropriate size for my pumpkin. I print out one copy to tape to the pumpkin, then use the same image on my smart phone as a reference while I carve. If you don't have a smart phone or tablet, you may want to print out two copies of your picture; one to tape to the pumpkin and one to use as a reference while you carve.

Step 1: Gather Tools

You'll need:

pumpkin-sized photograph of your subject
scissors
tape
pen
carbon paper
battery operated lights
knife
wood carving tools
rotary tool

Step 2: Cut and Scoop

Cut the top off of your pumpkin and scoop out the seeds and guts. Choose the best side of the pumpkin for carving, and then use a scooping tool or a spoon to thin that portion of the pumpkin from the inside. This makes the carving process much easier.

Step 3: Cut and Tape

Now you're ready to cut out your subject's face and a piece of carbon paper to roughly the same size. Tape the photograph and carbon paper together (carbon side out), then tape them to the pumpkin. Be sure that the dark side of the carbon paper is touching the pumpkin so your design will transfer nicely. You may have to fold or snip the edges of your photograph/carbon paper to get it to rest snugly against the pumpkin.

Step 4: Trace Tracy

Trace your subject (in my case Tracy Morgan) with a pen or other fine-pointed object like a wooden skewer. You must press firmly as you trace to ensure a good transfer from the carbon paper to your pumpkin. The goal here is to create a map on your pumpkin for carving, so trace all details including the outlines of shadows and highlights.

Step 5: Block in Basic Shapes

Using your wood carving tools, start carving the highlights, leaving shadows and other dark parts intact. The pumpkin skin will serve as the darkest parts of your carving, so do not disturb the skin at all on the darkest parts of your design. Lightly carve the midtones in as well.

Step 6: Light It Up

Once you have the basic shape shape carved out (highlights and midtones only), turn on your battery operated lights and place them in your pumpkin facing the side that you're carving.

Step 7: Carve in the Dark

Turn off the lights in your carving space and carve away! With the lights inside, the highlights will get brighter and brighter as you carve. Just be careful not to carve all the way through.

Step 8: Detail

Use your rotary tool for carving fine detail and small highlights, like the reflected light on your subject's eyes. Enjoy.

Introduction: Tracy Morgan-o-lantern